21193-80-6|(2R,3R,4S,5R)-2-(4-Amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol| Ambeed

Structure of Bromotubercidin
CAS No.: 21193-80-6

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Quality Control of [ 21193-80-6 ] Purity: 97% SDS Specification

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Product Details of [ 21193-80-6 ]

CAS No. :	21193-80-6
Formula :	C₁₁H₁₃BrN₄O₄
M.W :	345.15
SMILES Code :	O[C@H]1[C@H](N2C=C(Br)C3=C(N)N=CN=C32)O[C@H](CO)[C@H]1O
MDL No. :	N/A
InChI Key :	ZWTPRQXZXQEKFT-IOSLPCCCSA-N
Pubchem ID :	97186

Safety of [ 21193-80-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 21193-80-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 21193-80-6 ]

[ 21193-80-6 ] Synthesis Path-Downstream 1~35

1
[ 952429-11-7 ]
[ 21193-80-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ammonia; In methanol; at 120 - 130℃; for 16.0h;Sealed tube;	(2R,3R,4R,5R)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]-5-[5-bromo-4-chloro-7H-pyrrole[2,3-d]pyrimidin-7-yl]oxol-3-ylbenzoate (I-4, 7 g, 10.34 mmol) dissolved in ammonia in methanol (60 mL,In saturated with ammonia at 0 C) and placed in a sealed tube. The resulting solution was stirred at 120-130 C for 16 hours and the reaction mixture was concentrated in vacuo.The residue was purified by silica gel column chromatography (eluent: 1-10% methanol in dichloromethane), to give (2R,3R,4S,5R)-2-[4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-3,4-diol (I-5, 2.8 g, yield: 78%) as a white solid
72%	With ammonia; In methanol; at 100℃; for 4.0h;Sealed tube;	General procedure: The protected nucleoside 2a (473.8 mg, 700 mumol) was suspended in 30 mL 7M ammonia in methanol and heated at 100 C for 4 h in a sealed reaction vessel with stirring. After that, the solution was cooled to ambient temperature and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography sing dichloromethane/methanol (9:1) as eluent, to yield the product as colorless solid (174.0 mg, 504 mumol, 72%). 1H NMR(300 MHz, DMSO-d6) delta 8.10 (1H, s), 7.65 (1H, s), 6.82 (2H, br s), 6.04(1H, d, J=6.2 Hz), 5.35 (1H, d, J=6.5 Hz), 5.25-5.07 (2H, m),4.41-4.29 (1H, m), 4.12-4.02 (1H, m), 3.93-3.83 (1H, m), 3.67-3.47(2H, m); 13C NMR (75 MHz, DMSO-d6) delta 157.0, 152.4, 149.6, 121.8,101.1, 86.8, 86.7, 85.2, 73.9, 70.5, 61.5; HRMS (ESI): m/z calcd forC11H14BrN4O4 [M+H]+ 345.0193, found 345.0198.
40%	With ammonia; In methanol; at 120℃; for 2.0h;	A solution of (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (1) (870 mg, 1.29 mmol) in methanolic ammonia (7 N, 55 mL) was heated at 120 C in a screw-cap pressure flask for 2 h. The mixture was then cooled to rt, and the solvent evaporated under reduced pressure to afford the crude nucleoside. Purification by flash column chromatography (silica gel, 5-15% MeOH/CH2Cl2 gradient) provided (2) as an off-white solid (179 mg, 40%). TLC (silica gel, CH2Cl2/MeOH 6:1): Rf = 0.35. 1H NMR (500 MHz, DMSO-d6) delta: 8.10 (s, 1H, 6-H); 7.66 (s, 1H, 2-H); 6.81 (br s, 2H, 4-NH2); 6.05 (d, J = 6.0 Hz, 1H, 1'-H); 5.32 (d, J = 6.2 Hz, 1H, 2'-OH); 5.15 (d, J = 5.4 Hz, 1H, 3'-OH); 5.11 (d, J = 4.7 Hz, 1H, 5'-OH); 4.35 (m, 1H, 2'-H); 4.07 (m, 1H, 3'-H); 3.89 (m, 1H, 4'-H); 3.62 (m, 1H, 5'-H); 3.54 (m, 1H, 5'-H). LRMS (ESI): 346.2 and 344.4 [M+H]+.

	With ammonium hydroxide; In tetrahydrofuran; at 100℃; for 16.0h;Autoclave;	To a solution of intermediate 21 (6.6 g, 9.75 mmol ) in THF ( 130 niL) was added ammonia (28% in H20, 65 mL ) at room temperature. The reaction mixture was stirred at 100 C (using an autoclave) for 1 6 hours. The reaction mi ture cooled to room temperature and evaporated to dryness under reduced pressure. The residue was taken up into water ( 100 mL) and DCM ( 100 ml. ) and stirred for 1 hour. The layers were separated and the water layer was washed again with DCM ( 100 ml. ) to remove impurities. The water layer was filtered and the filtrate was evaporated to dryness. The residue was purified on flash chromatgraphy on silica (gradient eluention: DCM/MeOH from 95 :5 to 90: 10 ). The desired fractions were collected and the solvent was evaporated, yielding intermediate 22 (3.4 g, crude). The crude product was directly used for the next reaction step w ithout further purification.
6.81 g	With methanol; ammonia; In tetrahydrofuran; at 0 - 120℃; for 5.5h;Sealed tube;	i)355i A solution of 56d (20. g, 29 mrnoi) in methanol and THF (2:1, 180 mE) at 0 C in a pressure tube was purged with ammonia gas for 30 minutes. After sealing the tube, the mixture was heated at 120 C for 5 h. The mixture was cooled to RI?, concentrated under reduced pressure, and purified by FCC (Si02. 5-i5% MeOH in DCM) to afford 56e (681 g, 19 mmoi, 67% yield) as a light brown solid, ?H NMR (400 MHz. DMSO-d6): oe 8.09 (s, TH), 7.65 (s, 1H), 7.O0---6.60 (br, 21-1), 6.05 (d, J 6.16 Hz, IFI). 5.33 (d, J::: 6.36 FIz, 1H), 5.16---5.i 1(m, 2Ff), 4.33 (in, 1H), 4.06 (rn, 1H), 3.88 (in, 1H), 3.62 (m, 1H), 3.53 (m, 1H). LCMS purity: 97.6%; LRN?IS (ESI) rn/z caled fbr [M±Hj: 34502/347.02. Found: 345.02/347.02.

References: [1]Patent: CN109928998,2019,A .Location in patent: Paragraph 0200; 0205; 0206.
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1704 - 1713.
[3]Tetrahedron,2007,vol. 63,p. 9850 - 9861.
[4]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1787 - 1794.
[5]Patent: WO2017/32840,2017,A1 .Location in patent: Page/Page column 134.
[6]Patent: WO2018/85833,2018,A2 .Location in patent: Paragraph 0355.

2
C₉H₁₁BrClN₃Si [ No CAS ]
[ 21193-80-6 ]

References: [1]Tetrahedron,2007,vol. 63,p. 9850 - 9861.

3
[ 22276-95-5 ]
[ 21193-80-6 ]

References: [1]Tetrahedron,2007,vol. 63,p. 9850 - 9861.

4
[ 21193-80-6 ]
bromotubercidin 5'-monophosphate [ No CAS ]
[ 23197-94-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1481 - 1492.

5
[ 21193-80-6 ]
[ 1428254-19-6 ]

Yield	Reaction Conditions	Operation in experiment
61%		A solution of (2R,3R,4R,5R)-2-(4-Amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (2) (160 mg, 0.463 mmol) in hexamethylphosphoramide (2 mL) was cooled to 0 C. Thionyl chloride (0.202 mL, 2.78 mmol) was added dropwise with stirring, and after 10 min, the solution was warmed to rt and stirred a further 18 h. Following dilution with water (5 mL) and adjustment to pH 8 with aqueous NaOH solution (1 M), the aqueous layer was extracted with EtOAc (3 * 5 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the crude nucleoside. This material was then dissolved in CH2Cl2 and triturated with hexanes to produce a precipitate. The precipitate was collected by filtration, providing pure (3) as an off-white solid (102 mg, 61%). TLC (silica gel, CH2Cl2/MeOH 6:1): Rf = 0.45. LRMS (ESI): 362.1, 364.0 and 365.9 [M+H]+.
	With N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; at 0 - 20℃; for 18.1667h;Inert atmosphere;	A solution of 56e (3.51 g, 10 rnmol) in HMPA. (15 mE) under nitrogen atmosphere at 0 C was charged with thionyl chloride (7.3 g, 61 nunol, 4.5 mL) dropwise over 10 miii, then stirred at RI? for 18 h. The reaction mixture was cooled to 0 C, carefully quenched with water (15 mE), and treated with 1 M NaOH until an alkaline pH was obtained. The aqueous mixture was extracted with EtOAc (3x 250 mL). The organic fractions were combined and washed with ice cold water (500 mE), brine (500 mE). dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and purified b FCC (Si02, 5-*i0% MeOH in DCM) to afford 56f (1.0 g, 2.4 mmol. 24% yield) as white sohd. ECMS purity: 88%; LRMS (ESI) ni/z caicd for [MH-H]H: 362.99/364.98. Found: 363.06/365.05.

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1787 - 1794.
[2]Patent: WO2018/85833,2018,A2 .Location in patent: Paragraph 0356.

6
[ 21193-80-6 ]
[ 1428254-20-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1787 - 1794.

7
7-bromo-2',3',5'-tri-O-acetyltubercidin [ No CAS ]
[ 21193-80-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ammonia; In methanol; at 20℃; for 8.0h;Inert atmosphere;	NH3/MeOH (3 mL) was added to 2a (30 mg, 0.064 mmol) and the resulting clear solution was stirred at room temperature for 8 h. TLC showed complete conversion of substrate to a more polar product. Volatiles were evaporated and the residue was column chromatographed (10% MeOH in CHCl3) to give 2c (17.5 mg, 80%) as a white powder with NMR data as reported:S2 1H NMR delta 8.10(s, 1H, H2), 7.66 (s, 1H, H8), 7.28, (br s, 2H, NH2), 6.04 (d, 1H, J = 6.2 Hz, H1'), 5.34 (d, 1H, J = 6.4 Hz, 2'-OH), 5.13-5.19 (m, 2H, 3'-OH, 5'-OH) 4.34 (q, 1H, J = 6.1 Hz, H2'), 4.06 ("q", 1H, J= 4.8 Hz, H3'), 3.88 (q, 1H, J = 3.6 Hz, H4'), 3.58-3.64 (m, 1H, H5'), 3.49-3.56 (m, 1H, H5'').

References: [1]Tetrahedron Letters,2016,vol. 57,p. 4364 - 4367.

8
[ 60343-84-2 ]
[ 21193-80-6 ]

References: [1]Tetrahedron Letters,2016,vol. 57,p. 4364 - 4367.

9
[ 21193-80-6 ]
C₂₃H₂₂BrN₅O₄ [ No CAS ]

References: [1]Patent: WO2017/32840,2017,A1 .

10
[ 21193-80-6 ]
[ 77-76-9 ]
[(3aR,4R,6R,6aR)-6-[4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxolan-4-yl]methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In acetone; at 60℃; for 3.0h;	To a mixture of intermediate 22 ( 1 .0 g, crude) in acetone (32 mL) was added 2,2- dimethoxy propane (1.78 mL g. 14.5 mmol ) and 4-methy lbenzenesu 1 fo n ic acid (0.61 g, 3. 19 mmol) in one portion at room temperature. The mixture was stirred at 60 C for 3 hours. The mixture was cooled to room temperature and quenched by adding saturated aHCO; ( 10 niL) slowly and then extracted with ethyl acetate (50 mL x 5 ). The combined organic phase was washed with saturated brine (120 mL ), dried with MgS04, filtered and concentrated in vacuum, offered intermediate 23 (0.80 g, crude). The crude product was directly used for the next reaction step w ithout further purification.

References: [1]Patent: WO2017/32840,2017,A1 .Location in patent: Page/Page column 134; 135.

11
[ 21193-80-6 ]
(2R,3R,4S,5S)-2-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol [ No CAS ]

References: [1]Patent: WO2018/85833,2018,A2 .

12
[ 21193-80-6 ]
(2R,3R,4S,5S)2(4-amino-5-vinyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)5-((methylthio)methyl)tetrahydrofuran-3,4-diol [ No CAS ]

References: [1]Patent: WO2018/85833,2018,A2 .

13
[ 21193-80-6 ]
[ 69-33-0 ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 8589 - 8595.

14
[ 21193-80-6 ]
[ 329214-79-1 ]
4-amino-5-(pyridin-3-yl)-N7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine [ No CAS ]